This invention relates to certain sulfonylureas having amino-substituted heterocyclic rings which show selectivity for rape.
In U.S. Pat. No. 4,127,405, compounds are disclosed of the general formula: ##STR1## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, akyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n -- or CH.sub.3 CH.sub.2 S(O).sub.n --;
R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA0 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA0 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or akoxy of 1-2 carbon atom; PA0 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA0 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA0 W and Q are independently oxygen or sulfur; PA0 n is 0, 1 or 2; PA0 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA0 Y is methyl or methoxy; or their agriculturally suitable salts; provided that: PA0 R.sub.2 and R.sub.3 may be hydrogen, as may R.sub.4 and R.sub.5 ; PA0 R.sub.1 may be ##STR3## R.sub.2 is H, Cl, Br, F, C.sub.1 -C.sub.3 alkyl, --NO.sub.2, --SO.sub.2 CH.sub.3, --OCH.sub.3, --SCH.sub.3, --CF.sub.3, --N(CH.sub.3).sub.2, --NH.sub.2 or --CN; PA0 R.sub.3 is H, Cl, Br, F or CH.sub.3 ; PA0 R.sub.4 is H or --CH.sub.3 ; PA0 R.sub.5 is H, --CH.sub.3 or --OCH.sub.3 ; PA0 Z is N; PA0 X is H, Cl, --CH.sub.3, --OCH.sub.3, --OCH.sub.2 CH.sub.3 or --OCH.sub.2 CH.sub.2 OCH.sub.3 ; PA0 Y may be H; Cl; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted with --OCH.sub.3, --OC.sub.2 H.sub.5, --CN, --CO.sub.2 CH.sub.3, --CO.sub.2 C.sub.2 H.sub.5, or 1 to 3 atoms of F, Cl, Br; or NR.sub.16 R.sub.17 where R.sub.16 is H or CH.sub.3 and R.sub.17 may be H, OCH.sub.3 or C.sub.1 -C.sub.6 alkyl. PA0 2-[[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl] benzoic acid, methyl ester, m.p. 204.degree.-206.degree. C.; PA0 2-[[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl] benzoic acid, ethyl ester, m.p. 212.degree.-215.degree. C.; and PA0 N-[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)aminocarbonyl]-2-methylsulfon yloxybenzenesulfonamide, m.p. 178.degree.-180.degree. C.
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA1 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA1 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen.
In particular, the patent discloses orthosubstituted compounds wherein the substitution is C.sub.1 -C.sub.4 alkyl.
In U.S. Pat. No. 4,383,113, compounds are disclosed of the general formula: ##STR2## wherein R may be C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.10 alkenyl or C.sub.2 -C.sub.6 alkyl substituted with halogen;
U.S. Pat. No. 4,310,346, teaches herbicidal triazine sulfonylureas containing ortho-sulfamoyl groups.
EPO Publication No. 44,212 (published Jan. 20, 1982) teaches herbicidal triazine sulfonylureas containing ortho-sulfonate groups.
None of the above disclosures teaches compounds which are selective for rape.
Rape, also known as canola, is an annual broadleaf crop grown for its oil and use as a seed meal. Rape is a member of the genus Brassica and commonly includes Brassica napus (rape or oilseed rape) and Brassica campestris (fodder rape or turnip rape). Rape oil is used in a wide range of food products including ice cream, lard, margarine and chocolate. The extracted rape seed meal is used as a livestock feed.
The genus Brassica also includes other important crop plants such as broccoli, cauliflower, Brussel sprouts and cabbage.
With the current population explosion and concomitant world food shortage, improvements in efficiency of producing a crop such as rape is extremely important. Prevention or minimization of the loss of a portion of such a valuable crop by killing, or inhibiting the growth of undesired vegetation is one way of improving the crop yields.